CA2932844A1 - Composes formant des excimeres - Google Patents

Composes formant des excimeres Download PDF

Info

Publication number
CA2932844A1
CA2932844A1 CA2932844A CA2932844A CA2932844A1 CA 2932844 A1 CA2932844 A1 CA 2932844A1 CA 2932844 A CA2932844 A CA 2932844A CA 2932844 A CA2932844 A CA 2932844A CA 2932844 A1 CA2932844 A1 CA 2932844A1
Authority
CA
Canada
Prior art keywords
compound
sample
metal ion
protein
fluorescence
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA2932844A
Other languages
English (en)
Other versions
CA2932844C (fr
Inventor
Dziyana KRASKOUSKAYA
Patrick Thomas Gunning
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Toronto
Original Assignee
University of Toronto
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Toronto filed Critical University of Toronto
Publication of CA2932844A1 publication Critical patent/CA2932844A1/fr
Application granted granted Critical
Publication of CA2932844C publication Critical patent/CA2932844C/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/44—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/001—Pyrene dyes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6813—Hybridisation assays
    • C12Q1/6816—Hybridisation assays characterised by the detection means
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6842—Proteomic analysis of subsets of protein mixtures with reduced complexity, e.g. membrane proteins, phosphoproteins, organelle proteins
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2440/00—Post-translational modifications [PTMs] in chemical analysis of biological material
    • G01N2440/14—Post-translational modifications [PTMs] in chemical analysis of biological material phosphorylation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Physics & Mathematics (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Computational Biology (AREA)
  • General Physics & Mathematics (AREA)
  • Food Science & Technology (AREA)
  • Cell Biology (AREA)
  • Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Peptides Or Proteins (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

La présente invention concerne des composés formant des excimères de formule I:W-V-[Y]n W étant un fluorophore formant des excimères, V étant une fraction de liaison, Y étant une fraction de coordination aux ions métalliques et n ayant la valeur de 1, 2 ou 3. En particulier, l'invention porte sur des composés formant des excimères pour la détection de sites phosphorylés au plan proximal comprenant ceux présents sur les polypeptides, les protéines, le pyrophosphate et l'ARN, par exemple dans une solution aqueuse, dans des membranes de transfert sur gels de polyacrylamide, des essais sur support solide et dans des échantillons de culture de cellules.
CA2932844A 2013-12-19 2014-12-19 Composes formant des excimeres Active CA2932844C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361918256P 2013-12-19 2013-12-19
US61/918,256 2013-12-19
PCT/CA2014/000901 WO2015089639A1 (fr) 2013-12-19 2014-12-19 Composés formant des excimères

Publications (2)

Publication Number Publication Date
CA2932844A1 true CA2932844A1 (fr) 2015-06-25
CA2932844C CA2932844C (fr) 2023-02-21

Family

ID=53401848

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2932844A Active CA2932844C (fr) 2013-12-19 2014-12-19 Composes formant des excimeres

Country Status (3)

Country Link
US (1) US10889554B2 (fr)
CA (1) CA2932844C (fr)
WO (1) WO2015089639A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106872418B (zh) * 2015-12-11 2019-04-09 中国科学院大连化学物理研究所 检测磷酸化蛋白的荧光探针系统、探针合成方法及应用
CN106867516B (zh) * 2015-12-11 2019-02-01 中国科学院大连化学物理研究所 一种基于芘激基复合物的镉离子荧光探针及其制备方法和应用
KR102055660B1 (ko) * 2018-03-07 2019-12-13 경상대학교산학협력단 나프타미도-페닐아잔디일 유도체, 이를 포함하는 우라닐 이온 검출용 조성물 및 이를 이용한 우라닐 이온 검출 방법
US11977028B2 (en) * 2020-04-15 2024-05-07 Northwestern University Mechanical-bond-induced exciplex fluorescence
JP2022135780A (ja) * 2021-03-05 2022-09-15 野村マイクロ・サイエンス株式会社 被験物質の検出方法、検出試薬組成物、検出装置、精製水製造設備、注射用水製造設備、精製水製造方法及び注射用水製造方法
JP2023066177A (ja) * 2021-10-28 2023-05-15 野村マイクロ・サイエンス株式会社 エンドトキシン検出方法及びエンドトキシン検出装置、精製水製造設備及び注射用水製造設備、並びに精製水製造方法及び注射用水製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1665790A (zh) 2002-05-03 2005-09-07 莫莱丘莱尔探针公司 用于检测和分离磷酸化分子的组合物及方法

Also Published As

Publication number Publication date
CA2932844C (fr) 2023-02-21
US10889554B2 (en) 2021-01-12
US20160304473A1 (en) 2016-10-20
WO2015089639A1 (fr) 2015-06-25

Similar Documents

Publication Publication Date Title
CA2932844C (fr) Composes formant des excimeres
Baez et al. Mass spectrometry in studies of protein thiol chemistry and signaling: opportunities and caveats
JP4453363B2 (ja) アミノ官能性化合物の分析方法及び分析試薬
Maity et al. A metal-free fluorescence turn-on molecular probe for detection of nucleoside triphosphates
Romieu et al. The first comparative study of the ability of different hydrophilic groups to water-solubilise fluorescent BODIPY dyes
EP3160971B1 (fr) Procédé de détection sélective et d'estimation de l'histidine et de la cystéine
EP3262412B1 (fr) Enrichissement d'acides lysophosphatidiques par des matériaux polymères à matrice
CN106461649B (zh) 用于在细胞中标记蛋白质或其它生物分子的基于金属螯合的荧光探针
EP3545314A1 (fr) Réactifs et méthodes d'analyse de protéines et de métabolites ciblés par des sondes covalentes
Guo et al. A simple colorimetric and fluorescent probe with high selectivity towards cysteine over homocysteine and glutathione
WO2004078724A1 (fr) Procede de marquage d'un peptide phosphoryle, procede d'adsorption selective afferent, compose complexe utilise dans celui-ci, procede de preparation du compose complexe et compose de depart du compose complexe
US20230100536A1 (en) Intercellular and intracellular proximity-based labeling compositions and systems
CA3078142A1 (fr) Capteurs pour la detection de membranes contenant du phosphate chargees negativement et composants de membrane
EP3137898A2 (fr) Capteur moléculaire fluorescent permettant de cibler des modifications affectant la surface de protéines et ses procédés d'utilisation
KR20190055914A (ko) 하이드라지드 결합된 나프탈이미드 유도체 및 이의 구리 풀 이미징 용도
WO2013144656A1 (fr) Sondes à site actif
CA2720991A1 (fr) Nouvelles molecules de marquage optique en proteomique et autres analyses biologiques
JP4109621B2 (ja) リン酸モノエステル化合物の分子量を求める方法、およびマススペクトル測定用添加剤
Cilibrizzi et al. A tri-functional vanadium (iv) complex to detect cysteine oxidation
Cabral The Development of Assays for Detecting Proximal Phosphorylation and Covalent Modification of Proteins
Kraskouskaya Design and Development of Fluorescent Sensors for the Detection of Proximally Phosphorylated Peptide and Protein Motifs
TWI535710B (zh) 以苯并噁－１，３－二唑骨架爲主的化合物及偵測一待測品中是否存有生物硫醇的方法
AU2003296059A1 (en) Method for identifying molecular weight of a phosphoric acid monoester compound and an additive for mass spectrometry
US20240103005A1 (en) N-acryloylindoles and methods of use
Jia Chemical Imaging and Proteomics Approaches for Probing Copper and Histidine Biology

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20191217

EEER Examination request

Effective date: 20191217

EEER Examination request

Effective date: 20191217

EEER Examination request

Effective date: 20191217

EEER Examination request

Effective date: 20191217

EEER Examination request

Effective date: 20191217